Epicocconone
Chemical compound
From Wikipedia, the free encyclopedia
Epicocconone is a long Stokes' shift fluorogenic natural product found in the fungus Epicoccum nigrum.[1] Though weakly fluorescent in water (green emission, 520 nm) it reacts covalently yet reversibly with primary amines such as those in proteins to yield a product with a strong orange-red emission (610 nm).[2] Epicoconone is notable because it the first covalent/reversible/turn-on fluorophore to be discovered and is a natural product with a new fluorescent scaffold. It is also cell membrane permeable, unlike many other fluorophores, and subsequently can be used in in vivo (live cell) applications.[2] Additionally, this dye can be used as a sensitive total protein stain for 1D and 2D electrophoresis,[3] quantitative determination of protein concentration,[4] making it a powerful loading control for Western blots.[5]
| |
| Names | |
|---|---|
| Preferred IUPAC name
(6S,9aS)-6-(Hydroxymethyl)-3-[(1Z,4E,6E,8E)-1-hydroxy-3-oxodeca-1,4,6,8-tetraen-1-yl]-9a-methyl-5,6-dihydro-2H-furo[3,2-g][2]benzopyran-2,9(9aH)-dione | |
| Other names
Deep Purple Lava Purple | |
| Identifiers | |
3D model (JSmol) |
|
| ChEBI | |
| ChemSpider | |
PubChem CID |
|
| UNII | |
| |
| |
| Properties | |
| C23H22O7 | |
| Molar mass | 410.422 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
| |
Synthetic variant
In addition to the natural variant from the fungus, there are several synthetic analogs.[6] With respect to protein staining properties there are few differences between natural and synthetic analogs.
